CA2778171C - Bridged artificial nucleoside and nucleotide - Google Patents
Bridged artificial nucleoside and nucleotide Download PDFInfo
- Publication number
- CA2778171C CA2778171C CA2778171A CA2778171A CA2778171C CA 2778171 C CA2778171 C CA 2778171C CA 2778171 A CA2778171 A CA 2778171A CA 2778171 A CA2778171 A CA 2778171A CA 2778171 C CA2778171 C CA 2778171C
- Authority
- CA
- Canada
- Prior art keywords
- group
- carbon atoms
- compound
- amino
- substituents selected
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
- C12N15/111—General methods applicable to biologically active non-coding nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/10—Type of nucleic acid
- C12N2310/11—Antisense
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/32—Chemical structure of the sugar
- C12N2310/323—Chemical structure of the sugar modified ring structure
- C12N2310/3231—Chemical structure of the sugar modified ring structure having an additional ring, e.g. LNA, ENA
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2320/00—Applications; Uses
- C12N2320/50—Methods for regulating/modulating their activity
- C12N2320/51—Methods for regulating/modulating their activity modulating the chemical stability, e.g. nuclease-resistance
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Plant Pathology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009248979 | 2009-10-29 | ||
| JP2009-248979 | 2009-10-29 | ||
| JP2010023209 | 2010-02-04 | ||
| JP2010-023209 | 2010-02-04 | ||
| PCT/JP2010/068409 WO2011052436A1 (ja) | 2009-10-29 | 2010-10-19 | 架橋型人工ヌクレオシドおよびヌクレオチド |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2778171A1 CA2778171A1 (en) | 2011-05-05 |
| CA2778171C true CA2778171C (en) | 2017-07-25 |
Family
ID=43921860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2778171A Active CA2778171C (en) | 2009-10-29 | 2010-10-19 | Bridged artificial nucleoside and nucleotide |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8541562B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2495248B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JPWO2011052436A1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102596983B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010312751B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2778171C (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011052436A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012029870A1 (ja) * | 2010-08-31 | 2012-03-08 | 国立大学法人大阪大学 | オリゴヌクレオチド、およびオリゴヌクレオチドを有効成分として含有する脂質異常症治療剤 |
| US20140323709A1 (en) | 2011-12-12 | 2014-10-30 | National Cerebral And Cardiovascular Center | Oligonucleotide and therapeutic agent for hyperlipidemia containing same as active ingredient |
| TW201402594A (zh) | 2012-06-18 | 2014-01-16 | Daiichi Sankyo Co Ltd | 核苷類似物的製造中間體及其製造方法 |
| CA2885719C (en) * | 2012-09-21 | 2017-07-11 | Osaka University | Oligonucleotide and artificial nucleoside having guanidine bridge |
| WO2014109384A1 (ja) * | 2013-01-10 | 2014-07-17 | 塩野義製薬株式会社 | 架橋型核酸誘導体の製造方法 |
| JPWO2014112463A1 (ja) * | 2013-01-15 | 2017-01-19 | 国立大学法人大阪大学 | スルホンアミド構造を有するヌクレオシドおよびヌクレオチド |
| WO2014126229A1 (ja) | 2013-02-18 | 2014-08-21 | 塩野義製薬株式会社 | 含窒素複素環構造を有するヌクレオシド及びヌクレオチド |
| WO2015020194A1 (ja) * | 2013-08-09 | 2015-02-12 | 国立大学法人大阪大学 | Acsl1に対するアンチセンスオリゴヌクレオチド |
| GB201410693D0 (en) | 2014-06-16 | 2014-07-30 | Univ Southampton | Splicing modulation |
| US20170211073A1 (en) * | 2014-07-10 | 2017-07-27 | Kenji Nakano | Antisense antineoplastic agent |
| KR102620328B1 (ko) | 2014-10-03 | 2024-01-02 | 콜드스프링하버러보러토리 | 핵 유전자 산출량의 표적화 증강 |
| JP2018140938A (ja) * | 2015-07-24 | 2018-09-13 | 日産化学株式会社 | 人工ヌクレオシド及び人工ヌクレオチド並びに人工オリゴヌクレオチド |
| TW201718618A (zh) * | 2015-09-18 | 2017-06-01 | 田邊三菱製藥股份有限公司 | 架橋型核酸GuNA,其製造方法,及中間體化合物 |
| KR20220105174A (ko) | 2015-10-09 | 2022-07-26 | 유니버시티 오브 사우스앰톤 | 유전자 발현의 조절 및 탈조절된 단백질 발현의 스크리닝 |
| CN109312343B (zh) | 2015-12-14 | 2022-09-27 | 冷泉港实验室 | 用于治疗常染色体显性精神发育迟滞5型和Dravet综合征的反义寡聚体 |
| US11096956B2 (en) | 2015-12-14 | 2021-08-24 | Stoke Therapeutics, Inc. | Antisense oligomers and uses thereof |
| EP3415524A4 (en) * | 2016-01-07 | 2019-09-04 | Osaka University | INHIBITOR OF α-SYNNUCLEINE EXPRESSION |
| AU2017211461B2 (en) | 2016-01-26 | 2023-01-12 | Nissan Chemical Corporation | Single-stranded oligonucleotide |
| EP3418289A4 (en) | 2016-02-17 | 2019-10-30 | Tokyo Institute of Technology | ARTIFICIAL NUCLEOSIDE AND ARTIFICIAL NUCLEOTIDE AND ARTIFICIAL OLIGONUCLEOTIDE |
| WO2018009466A1 (en) | 2016-07-05 | 2018-01-11 | Aduro Biotech, Inc. | Locked nucleic acid cyclic dinucleotide compounds and uses thereof |
| JP2020055750A (ja) * | 2017-01-30 | 2020-04-09 | 賢二 中野 | 癌浸潤または転移阻害核酸薬 |
| CA3052801A1 (en) | 2017-02-06 | 2018-08-09 | Nissan Chemical Corporation | Single-stranded oligonucleotide |
| WO2018155450A1 (ja) | 2017-02-21 | 2018-08-30 | 国立大学法人大阪大学 | アンチセンスオリゴ核酸 |
| JP7138349B2 (ja) * | 2017-02-21 | 2022-09-16 | 国立大学法人大阪大学 | 核酸化合物およびオリゴヌクレオチド |
| US11638717B2 (en) | 2017-03-29 | 2023-05-02 | Shionogi & Co., Ltd. | Complex of nucleic acid medicine and multibranched lipid |
| JP7141621B2 (ja) | 2017-03-31 | 2022-09-26 | 学校法人 愛知医科大学 | コンドロイチン硫酸生合成を阻害するアンチセンス核酸 |
| EP3633036A4 (en) | 2017-05-26 | 2021-03-17 | National Cerebral and Cardiovascular Center | NUCLEIC ACID TARGETING ANTI-SENSES PCSK9 |
| EP3628737A4 (en) | 2017-07-05 | 2021-01-20 | Osaka University | ENA-ANTISENSE-OLIGONUCLEOTIDE TO INHIBIT ALPHA-SYNUCLEIN EXPRESSION |
| WO2019009298A1 (ja) * | 2017-07-05 | 2019-01-10 | 国立大学法人大阪大学 | α-シヌクレイン発現抑制剤 |
| AU2018307294B2 (en) | 2017-07-26 | 2025-04-17 | Nissan Chemical Corporation | Single-stranded oligonucleotide |
| SMT202400071T1 (it) | 2017-08-25 | 2024-03-13 | Stoke Therapeutics Inc | Oligomeri antisenso per il trattamento di condizioni e malattie |
| JP7177446B2 (ja) | 2017-08-31 | 2022-11-24 | 田辺三菱製薬株式会社 | Il-33アンタゴニストを含む子宮内膜症治療剤 |
| AU2019237599A1 (en) | 2018-03-20 | 2020-11-12 | Nissan Chemical Corporation | Antisense oligonucleotide having reduced toxicity |
| US12060558B2 (en) | 2018-05-04 | 2024-08-13 | Stoke Therapeutics, Inc. | Methods and compositions for treatment of cholesteryl ester storage disease |
| CN112513062B (zh) * | 2018-07-31 | 2024-05-10 | 国立大学法人大阪大学 | 含有寡聚核苷酸的小细胞肺癌治疗药 |
| EP3967328A4 (en) | 2019-03-29 | 2022-12-28 | Sysmex Corporation | NEW ARTIFICIAL NUCLEIC ACID, METHOD FOR MAKING IT, AND USE THEREOF |
| SG11202112741XA (en) | 2019-05-31 | 2021-12-30 | Aligos Therapeutics Inc | Modified gapmer oligonucleotides and methods of use |
| EP4005602A4 (en) | 2019-07-30 | 2024-06-12 | Shionogi & Co., Ltd | NUCLEIC ACID AGENT TARGETED AGAINST MURF1 |
| WO2021039879A1 (ja) | 2019-08-27 | 2021-03-04 | 国立大学法人東海国立大学機構 | 胃癌分子標的核酸医薬 |
| WO2021127406A1 (en) * | 2019-12-19 | 2021-06-24 | The Regents Of The University Of California | Methods of producing target capture nucleic acids |
| WO2021132648A1 (ja) * | 2019-12-27 | 2021-07-01 | ルクサナバイオテク株式会社 | Recqlの発現を阻害するアンチセンスオリゴヌクレオチド及びその用途 |
| WO2021177267A1 (ja) | 2020-03-02 | 2021-09-10 | 田辺三菱製薬株式会社 | miR-33b阻害物質による動脈瘤の予防または治療 |
| CN115485381A (zh) | 2020-03-26 | 2022-12-16 | 国立研究开发法人国立循环器病研究中心 | 以apoc3为靶点的反义核酸 |
| WO2021216785A1 (en) | 2020-04-21 | 2021-10-28 | Flagship Pioneering, Inc. | Bifunctional molecules and methods of using thereof |
| CA3173647A1 (en) | 2020-05-11 | 2021-11-18 | Isabel AZNAREZ | Opa1 antisense oligomers for treatment of conditions and diseases |
| EP4219517A4 (en) | 2020-09-25 | 2024-09-25 | Riken Genesis Co., Ltd. | NOVEL ARTIFICIAL NUCLEIC ACID, METHOD FOR PRODUCING THE SAME AND USE THEREOF |
| WO2022097727A1 (ja) | 2020-11-06 | 2022-05-12 | 住友ファーマ株式会社 | Rps25遺伝子の発現及び/又は機能調節剤 |
| WO2022181807A1 (ja) | 2021-02-25 | 2022-09-01 | 国立大学法人大阪大学 | REST mRNA前駆体のプロセシングにおけるNエキソンのスキッピングを誘導するオリゴヌクレオチド |
| EP4331606A4 (en) | 2021-04-30 | 2025-05-07 | Kyoto University | PREVENTION OR TREATMENT OF MYOPATHY USING A MIR-33B INHIBITOR |
| US20240247263A1 (en) | 2021-05-06 | 2024-07-25 | Luxna Biotech Co., Ltd. | Method for designing oligonucleotide having reduced central toxicity |
| KR20240013202A (ko) | 2021-05-28 | 2024-01-30 | 스미토모 파마 가부시키가이샤 | 안티센스 핵산 |
| EP4389893A4 (en) | 2021-08-21 | 2025-09-10 | Takeda Pharmaceuticals Co | PEPTIDE-DRUG CONJUGATE BINDING HUMAN TRANSFERRIN RECEPTOR |
| JPWO2023127857A1 (cg-RX-API-DMAC7.html) | 2021-12-27 | 2023-07-06 | ||
| EP4495242A1 (en) | 2022-03-17 | 2025-01-22 | Aichi Medical University | Antisense nucleic acid capable of inhibiting biosynthesis of chondroitin sulfate |
| CN120187739A (zh) | 2022-11-10 | 2025-06-20 | 璐库萨那生物技术株式会社 | 桥联部具有胍基结构的修饰核苷和使用其的寡核苷酸的制造方法 |
| JPWO2024181416A1 (cg-RX-API-DMAC7.html) | 2023-02-28 | 2024-09-06 | ||
| WO2024257847A1 (ja) | 2023-06-16 | 2024-12-19 | 住友ファーマ株式会社 | Rps25遺伝子の発現及び/又はその機能を調節するアンチセンスオリゴヌクレオチド |
| WO2025005265A1 (ja) * | 2023-06-30 | 2025-01-02 | 日産化学株式会社 | 毒性が低減されたアンチセンスオリゴヌクレオチド |
| US20250368996A1 (en) | 2024-05-14 | 2025-12-04 | Aligos Therapeutics, Inc. | Modified antisense oligonucleotides for treating hepatitis b virus |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3756313B2 (ja) | 1997-03-07 | 2006-03-15 | 武 今西 | 新規ビシクロヌクレオシド及びオリゴヌクレオチド類縁体 |
| HRP20000751A2 (en) | 1998-05-26 | 2001-12-31 | Icn Pharmaceuticals | Novel nucleosides having bicyclic sugar moiety |
| US7615619B2 (en) | 2002-02-13 | 2009-11-10 | Takeshi Imanishi | Nucleoside analogues and oligonucleotide derivative comprising nucleotide analogue thereof |
| US7427672B2 (en) | 2003-08-28 | 2008-09-23 | Takeshi Imanishi | Artificial nucleic acids of n-o bond crosslinkage type |
| WO2012029870A1 (ja) * | 2010-08-31 | 2012-03-08 | 国立大学法人大阪大学 | オリゴヌクレオチド、およびオリゴヌクレオチドを有効成分として含有する脂質異常症治療剤 |
-
2010
- 2010-10-19 JP JP2011538366A patent/JPWO2011052436A1/ja not_active Ceased
- 2010-10-19 CA CA2778171A patent/CA2778171C/en active Active
- 2010-10-19 EP EP10826568.7A patent/EP2495248B1/en active Active
- 2010-10-19 WO PCT/JP2010/068409 patent/WO2011052436A1/ja not_active Ceased
- 2010-10-19 CN CN201080049279.2A patent/CN102596983B/zh active Active
- 2010-10-19 AU AU2010312751A patent/AU2010312751B2/en active Active
- 2010-10-19 US US13/502,611 patent/US8541562B2/en active Active
-
2013
- 2013-11-27 JP JP2013244692A patent/JP5669073B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2495248B1 (en) | 2017-01-11 |
| EP2495248A4 (en) | 2013-10-16 |
| CN102596983A (zh) | 2012-07-18 |
| US8541562B2 (en) | 2013-09-24 |
| EP2495248A1 (en) | 2012-09-05 |
| WO2011052436A1 (ja) | 2011-05-05 |
| JP5669073B2 (ja) | 2015-02-12 |
| CA2778171A1 (en) | 2011-05-05 |
| AU2010312751B2 (en) | 2014-07-24 |
| JPWO2011052436A1 (ja) | 2013-03-21 |
| US20120208991A1 (en) | 2012-08-16 |
| CN102596983B (zh) | 2016-06-15 |
| AU2010312751A1 (en) | 2012-06-14 |
| JP2014043462A (ja) | 2014-03-13 |
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